"Road to Rupert" is the ninth episode of the fifth season of Family Guy. The episode follows Brian after he inadvertently sells Stewie's teddy bear, Rupert, during a yard sale. In an attempt to retrieve him, Stewie and Brian travel across the United States, eventually discovering he is with a child living in Aspen, Colorado. Meanwhile, Peter has his driving license revoked for careless driving and is forced to be driven around by Meg, which annoys him.

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The Griffins have a yard sale to sell off household items that they no longer need, but Brian accidentally sells Stewie's teddy bear, Rupert, causing Stewie to think Rupert has been kidnapped. Brian takes Stewie to the toy store to try to find a replacement, but ends up admitting he accidentally sold it, after which Stewie exclaims: "You son of a bitch!". He attempts to retrieve Rupert by tracking DNA samples against the federal database from the money Brian was paid for Rupert. They discover the man who bought Rupert lives in Quahog, but upon arrival—they discover the house is deserted. After seeing the moving truck and following it, with Mayor West driving, they discover the man now resides in Aspen, Colorado, meaning West drives them no further, only stopping in the Connecticut state line. To get over the mountains, the pair rent a helicopter after discovering "to rent a helicopter, you can pay with cash, check, or a jaunty tune". Stewie then performs a dance for the man in the office (with help from Gene Kelly), but when Brian crashes the helicopter into the mountain, the two end up next to the entrance to Aspen.

Reluctant to give Rupert back to Stewie, Stanford Cordray (the buyer, voiced by Rob Lowe) and his family organize a skiing race down the mountain, so if Stewie is the first down, they are allowed to take Rupert away with them and if Stanford wins, he can have Brian. Stewie cheats by installing rockets in his skis, and relaxes to watch his progress. Stewie then crashes into a tree and loses the race. He tells Brian that maybe this means he should give up Rupert, but he proceeds to grab Rupert after telling his personal butler Crohn to throw a cup of hot tea on the child's face, forcing him to drop the bear. The two make a run for it before the child's parents notice, then realize they still need to get back to Quahog (which, by looking at a highway sign at the end, is 2112 miles away, a reference to the Rush 1976 album), so they carjack a passing driver in the city and drive home.

Meanwhile, Peter purchased his own Evel Knievel gloves at his own yard sale. He decides to use the family car to jump over a row of cars, but is unsuccessful and results in his drivers license being revoked by Joe. Lois arranges for Meg to become Peter's personal driver, and he makes numerous attempts to annoy Meg, including setting her hat on fire when traveling with his friends. When another car rear ends her and she is insulted by the driver, Meg takes out her repressed rage with Peter on the driver by beating him up; Peter is impressed, and the two bond in the car. In the end, Joe stops by Peter's house to reinstate his license. Meg worries that Peter will begin treating her badly again, but Peter says that while he will only do so in front of the family to keep up appearances, and that they will now be "secret best friends."[1]

This episode was written by Patrick Meighan, in his first episode of the season, and, like all Road to.. episodes from 2000–2007, directed by Dan Povenmire, in his second episode of the season.

Lois mocking Stewie Griffin: The Untold Story (or, as it's called in the scene, Stymie Gruffin: The Untold Story), citing the movie as a middle finger to the audience by being three episodes slapped together under the guise of a movie (followed by Brian calling in two bodyguards in suits to take Lois away) was edited on TV for time reasons.[2][3] A deleted scene showed one of Peter's crimes being a hate crime, where during his stunt he hit a car with a Jewish driver. The televised scene changed the Jewish driver to a female virgin driver and the crime being a rape (her tailpipe having busted her hymen) and not a hate crime.[3][4] The scene of Stewie getting high on NyQuil to cope with losing Rupert and mistaking a throw pillow for a cat was cut from TV airings for time reasons.[3][4]David Goodman noted that he feels the production crew may not have succeeded on this episode as everything falls into place easily,[3] such as the box falling out of the moving truck.[3] Every frame when Stewie is dancing in a montage of Anchors Aweigh took a large amount of work to produce.[2][5]

The montage of Stewie and Brian visiting several U.S. states (all of which are states where there's nothing but cornfields) was a DVD exclusive scene, removed from television for timing purposes.[2][6] This scene was partially based on series creator Seth MacFarlane traveling the United States after the September 11, 2001 attacks and realizing there is lots of corn throughout the U.S.[2] A deleted scene directly after the helicopter crash had shown Stewie saying "come here, puss" for a second time, but this was replaced with another.[2][4] Stewie and Brian carjacking somebody was added to the episode in a later rewrite and censored on television.[4]

When speaking with Brian at the yard sale, Lois comments that Stewie Griffin: The Untold Story is not a real movie, rather just three individual episodes together, but altering the title to Stymie Gruffin: The Untold Story when discussing it with Brian.[2]

Peter watches an episode of SpongeBob SquarePants in the car which features "The Campfire Song" performed in the actual episode. It had been written by Dan Povenmire for the original SpongeBob episode, but it was allowed in the episode as Nickelodeon gave Family Guy permission to reproduce the music.[6]

The entire scene of Stewie singing and dancing in order to secure rental of the helicopter is a reference to the 1945 musical film Anchors Aweigh.[2] The reflection of the original character (Jerry Mouse from Tom and Jerry) can be seen on the floor.

In a slight improvement over the previous week, the episode was viewed in 8.8 million homes in its original airing, according to Nielsen ratings. The episode also acquired a 3.1 rating in the 18–49 demographic, slightly edging out both The Simpsons and American Dad!.[7]

The episode received mixed comments from TV Squad, with Brett Love commenting that "the suspended license plot was a little thin, but that's forgivable given that this was the b-story for the episode, and there are only 22 minutes to work with."[8] Love comments positively on the Stewie and Brian relationship in the episode, commenting that, "the Stewie and Brian story is what made the episode for me. It was very well done, right down to the goofy little details."[8]IGN commented that, "...for Family Guy to have a great episode, it takes a good story and humorous "manatee" gags. "Road to Rupert" was able to deliver on both these fronts, with the majority of the episode's attention focused on Stewie and Brian's road story, meshed with many laugh out loud gags."[9]